Hydrazine → Benzopyrano[4,3,2-de]phthalazine

HRID 969288Notes

Reaction equation

HRID 969288 reaction equation
CO[C:3]([C:5]1[C:18]2[C:17](=O)[C:16]3[C:11](=[CH:12][CH:13]=[C:14](C)[CH:15]=3)[O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=O.[NH2:21][NH2:22]>>[N:21]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[O:10][C:9]3[C:18]=2[C:5]([CH:6]=[CH:7][CH:8]=3)=[CH:3][N:22]=1

Participants

3

Reactant 2

HCID 9321HydrazineHCID 21304614Methyl 7-methyl-9-oxo-9H-xanthene-1-carboxylate

Product 1

HCID 22731913Benzopyrano[4,3,2-de]phthalazine

Procedure

Prepared from the compound 11 (R═H) and 1.5 equivalent of hydrazine to give benzopyrano[4,3,2-de]phthalazine according to General Procedure C. To a solution of 0.3 g of benzopyrano[4,3,2-de]phthalazine in 7.5 mL of concentrate sulfuric acid is dropwise added 2.0 mL of fuming sulfuric acid at 0° C. The mixture is stirred for 3 hours at 0° C. and poured into 100 mL of ice-cold water. The precipitation is collected by filtration, washed with water to give of a white solid product, mp>300° C. (dec.). 1H-NMR (400 MHz, DMSO-d6); 12.7 (s, 1H), 8.35 (s, 1H), 7.92-7.90 (m, H), 7.76-7.71 (m, 2H), 7.38 (d, 1 H).

Sources & evidence

ORD record
ord-e8ff01aeb7434135ba364da207a44194
Source dataset
uspto-grants-2007_12
Patent number
US07307080B2

Reaction notes

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